| Identification | Back Directory | [Name]
TUBERCIDIN | [CAS]
69-33-0 | [Synonyms]
b120121
u-10071
CS-2599
ski26996
nsc56408
TUBERCIDIN
Aids051983
Aids-051983
TUBERCIDINE
sparsomycina
Sparsamycin A
Sparsomycine A
7-Deazadenosine
Tubercidin, >97%
7-DEAZAADENOSINE
7-deaza-adenosin
antibiotic155b2t
antibioticxk101-1
N7-Deazaadenosine
7-Deaza-adeonsine
7-Deaza-D-adenosine
TUBERCIDIN USP/EP/BP
Tubercidin (7-Deazaadenosine
7-deaza-adenosin(Tubercidine)
tubercidin from streptomyces tubercidicus
tubercidin from streptomyces*tubercidicus
7-Deazaadenosine, Tubercidin, Sparsomycine A
4-Amino-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
7H-Pyrrolo[2,3-d]pyrimidin-4-amine,7-b-D-ribofuranosyl-
4-Amino-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine
7H-Pyrrolo[2,3-d]pyrimidin-4-amine, 7-β-D-ribofuranosyl-
3-d)pyrimidin-4-amine,7-beta-d-ribofuranosyl-7h-pyrrolo(
3-d)pyrimidine,4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(
4-amino-7-(beta-d-ribofuranosyl)-pyrrolo(2,3-d)pyrimidine
4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(2,3-d)pyrimidine
7-beta-d-ribofuranosyl-7h-pyrrolo(2,3-d)pyrimidine-4-amine
7-beta-CD-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
4-AMINO-7-BETA-D-RIBOFURANOSYL-7H-PYROLLO(2,3-D)PYRIMIDINE
7H-Pyrrolo2,3-dpyrimidin-4-amine, 7-.beta.-D-ribofuranosyl-
7-.beta.-D-ribofuranosyl-7H-pyrrolo-[2,3-d]pyrimidin-4-amine
7H-Pyrrolo(2,3-D)pyrimidine, 4-amino-7-beta-D-ribofuranosyl-
7-Deazaadenosine, XK 101-1, NSC 56408, SparsoMycin A, U 10071
2-(4-aMinopyrrolo[2,3-d]pyriMidin-7-yl)-5-(hydroxyMethyl)oxolane-3,4-diol
(2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol | [EINECS(EC#)]
200-703-4 | [Molecular Formula]
C11H14N4O4 | [MDL Number]
MFCD00056012 | [MOL File]
69-33-0.mol | [Molecular Weight]
266.25 |
| Chemical Properties | Back Directory | [Melting point ]
247-248 °C (decomp)(Solv: water (7732-18-5)) | [alpha ]
D17 -67° (50% acetic acid) | [Boiling point ]
409.46°C (rough estimate) | [density ]
1.2896 (rough estimate) | [refractive index ]
1.8340 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Soluble in DMSO | [form ]
powder | [pka]
12.44±0.70(Predicted) | [color ]
off-white | [Merck ]
13,9875 | [BRN ]
38498 | [Stability:]
Hygroscopic | [InChIKey]
HDZZVAMISRMYHH-UIRWVKCDSA-N | [CAS DataBase Reference]
69-33-0 |
| Safety Data | Back Directory | [Hazard Codes ]
T+ | [Risk Statements ]
28 | [Safety Statements ]
36/37/39-45 | [RIDADR ]
UN 3462 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
UY8870000
| [F ]
10 | [HazardClass ]
6.1(a) | [PackingGroup ]
II | [HS Code ]
29419090 | [Toxicity]
LD50 i.v. in mice: 45 mg/kg (Anzai) |
| Hazard Information | Back Directory | [Chemical Properties]
White crystal | [Uses]
Tubercidin is a nucleoside metabolite first isolated from Streptomyces tubericidus. Tubercidin, like other nucleosides, is a broad spectrum potent chemotherapeutic agent active against viruses, bacteria, fungi, protozoans and tumors. Tubercidin acts on a diverse range of targets, such as RNA processing, nucleic acid and protein synthesis, and acts as a nucleoside mimic of adenosine. | [Uses]
Tubercidin is a nucleoside metabolite first isolated from Streptomyces tubericidus. Tubercidin, like other nucleosides, is a broad spectrum, potent chemotherapeutic agent active against viruses, bacteria, fungi, protozoans and tumours. Tubercidin acts at a diverse range of sites, such as RNA processing, nucleic acid and protein synthesis, and acts as a nucleoside mimic of adenosine. | [Definition]
ChEBI: An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus. | [Biological Activity]
tubercidin is an adenosine analog antibiotic agent.nucleoside antibiotics are a family of natural products with various biological functions. their biosynthesis is a complex process via multistep enzymatic reactions. | [in vitro]
previous study showed that tubercidin alone had a dose-dependent inhibitory effect on myeloid and erythroid human bone marrow progenitor cells. bfu-e were more sensitive at higher doses of tubercidin than cfu-gm. the 99% complete inhibition of bfu-e colonies was observed at 10 nm tubercidin, whereas complete inhibition of cfu-gm occurred at 100 nm [1]. | [in vivo]
animal toxicity study showed that four successive daily injections of tubercidin at 5 mg/kg per day could produce 100% mouse mortality within 3 to 5 days, with massive peritonitis and intestinal obstruction. in addition, coadministration of nbmpr-p at 25 mg/kg per day could protect the mice from the tubercidin lethality and allow the repetition of the regimen for a second time with 100% survival [1]. | [IC 50]
3.4 and 3.7 nm for granulocyte-macrophage cfu (cfu-gm) and erythroid burst-forming units (bfu-e), respectively | [storage]
Store at -20°C | [Purification Methods]
7-Deazaadenosine forms needles from hot H2O. It is soluble in H2O (0.33%), MeOH (0.5%) and EtOH (0.05%). It has UV max at 270nm ( 12,100) in 0.001N NaOH. The picrate has m 229-231o(dec). [Tolman et al. J Am Chem Soc 91 2102 1969, Mizuno et al. J Org Chem 28 3329 1963, IR: Anzai et al. J Antibiot (Japan) [9] 10 201 1957, Beilstein 26 IV 1117.] | [References]
[1] el kouni mh,diop d,o'shea p,carlisle r,sommadossi jp. prevention of tubercidin host toxicity by nitrobenzylthioinosine 5'-monophosphate for the treatment of schistosomiasis. antimicrob agents chemother.1989 jun;33(6):824-7.
[2] grage tb,rochlin db,weiss aj,wilson wl. clinical studies with tubercidin administered after absorption into human erythrocytes. cancer res.1970 jan;30(1):79-81. |
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